That is always the most interesting question. What are the criteria? There is a difference between an "I won lots of medals" all-star and a "I gave exquisite performances" all-star. I am sure that pangtongfan would concede that Patrick Chan is the all-time "read the protocols" champion, but not so much the all-time "look at my on-ice performances" champion.

For me, I would give heavy weight to what the skaters accomplished after their days of amateur competitions were over. Sonia Henie brought figure skating to hollywood. Dick Button was Mr. Figure Skating for half a century. Kurt Browning and Kristi Yamaguchi were better as professional entertainers than as amateur competitors. Scott Hamilton was a better entrepreneur and impresario than a skater. And Michelle Kwan wins the lifetime achievement award in the category of overall Kwanliness.

I like that idea, Math, of considering what skaters did after their amateur careers. Dick Button also had a good criterion: that a great skater left skating better than it was when he/she came in. So despite the fact that Sonia Henie's skating looked old-fashioned by the 1970s, she advanced the sport in several ways, including doing more demanding jumps than ladies ever did. As a pro skater, she also made skating attractive to larger audiences, both with her films and with her live shows. Without Henie, one might argue that skating would just have been a niche sport like dressage, interesting mainly to the families of people who had the money to train for years. Similarly, Button also advanced the jumps, and then later he did a lot of impresario work as well as his commentating on TV. He increased audiences and educated them as well.

I feel like lynn would be more a sentimental favorite for certain people. I'm not sure if she really belongs in the top 10.

By sentimental favorite I think you mean people are basing it off of emotion rather than facts, right? But since skating is half sport, half art, it's a given that sentiment/emotion is very important when critiquing a skater's legacy. When people think of skating "artists" through the ages, Janet is one of the first names to come up.
I'll be honest, despite all of her titles, I can't watch a Sonia Henie video without rolling my eyes and then having my mind wander off thinking about her Nazi ties. On the other hand, I can enjoy watching Peggy Fleming or Janet Lynn because as simple as their routines are, they're extremely graceful. Their skating has aged very well through the years. Medals and accomplishments are one very valid way to measure a skater's historical greatness, but I think that their legacy of performances is just as important. Of course one could also argue that we're not giving enough credit to skaters whose strengths were in figures, but I think the point is that skaters like Janet paved the way for skating's current freeskate-centric system and made figures obsolete.

PS I don't mean to downplay Sonia Henie's achievements and influence on the sport. Objectively she's one of the top 5 if not #1. I just can't stand watching her skate.

This is so hard to do , it comes down to personal taste and knowledge of skating and the progression of the sport . I have been watching old videos and am very surprised at some of the skaters from the late 70's to early 80,s . I think Denise Biellman would have dominated the sport if she would have stayed amateur , she was so spectacular with her jumps and was still improving when she left . Also I really wasn't a huge Robin Cousins fan at the time but when I look back he was one of the best complete skater that had it all ! Some of these lists are just personal favourites . Last comment would be to all the Chan haters , he is so good it is not even worth arguing !!!

By sentimental favorite I think you mean people are basing it off of emotion rather than facts, right? But since skating is half sport, half art, it's a given that sentiment/emotion is very important when critiquing a skater's legacy. When people think of skating "artists" through the ages, Janet is one of the first names to come up.

Clearly different parts of skating speak to us when judging the greatness of skater. Perhaps I am inclined to place more emphasis on the athletic aspects of skating than you are. These lists are after all, subjective for the most part. For myself, Lynn is enjoyable enough to watch. There is goodness to her skating, but it doesn't speak greatness to me. Unlike some others on this board, I do not find myself being entranced by it. I understand that she may have helped bring about the end of figures, but that is something I look at neutrally. I see it as neither a positive nor a negative.

Perhaps there should be separate lists for greatest athletic skaters and greatest artistic skaters?